EP1686953A2 - Systeme gelifiant pour huiles transparentes - Google Patents
Systeme gelifiant pour huiles transparentesInfo
- Publication number
- EP1686953A2 EP1686953A2 EP04819057A EP04819057A EP1686953A2 EP 1686953 A2 EP1686953 A2 EP 1686953A2 EP 04819057 A EP04819057 A EP 04819057A EP 04819057 A EP04819057 A EP 04819057A EP 1686953 A2 EP1686953 A2 EP 1686953A2
- Authority
- EP
- European Patent Office
- Prior art keywords
- silica
- fatty acid
- ester
- gellant
- composition
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
Links
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/19—Cosmetics or similar toiletry preparations characterised by the composition containing inorganic ingredients
- A61K8/25—Silicon; Compounds thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
- A61K8/04—Dispersions; Emulsions
- A61K8/042—Gels
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/60—Sugars; Derivatives thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/60—Sugars; Derivatives thereof
- A61K8/602—Glycosides, e.g. rutin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/60—Sugars; Derivatives thereof
- A61K8/604—Alkylpolyglycosides; Derivatives thereof, e.g. esters
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
- A61K8/84—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
- A61K8/86—Polyethers
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q1/00—Make-up preparations; Body powders; Preparations for removing make-up
- A61Q1/02—Preparations containing skin colorants, e.g. pigments
- A61Q1/04—Preparations containing skin colorants, e.g. pigments for lips
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q1/00—Make-up preparations; Body powders; Preparations for removing make-up
- A61Q1/02—Preparations containing skin colorants, e.g. pigments
- A61Q1/04—Preparations containing skin colorants, e.g. pigments for lips
- A61Q1/06—Lipsticks
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
- A61K2800/20—Chemical, physico-chemical or functional or structural properties of the composition as a whole
- A61K2800/26—Optical properties
- A61K2800/262—Transparent; Translucent
Definitions
- the invention relates to the field of cosmetics. More specifically, the invention relates to a gelling system for cosmetic oils.
- the long- wearing products on their own can be drying and uncomfortable on the lips, with a dull finish, thereby requiring a moisturizing topcoat to be applied over them.
- Such topcoats are difficult to formulate, since they need to be sufficiently incompatible with the base coat, which is frequently based on non-polar hydrocarbons and silicones, to prevent interference with the base coat's wear, and at the same time, are preferably transparent to give the best level of glossy appearance to the lips.
- the currently available topcoat products are opaque sticks that produce a small amount of shine.
- lip gloss products intended to provide high shine it is difficult to achieve the desired level of transparent gloss without producing a product that is too liquid or oily.
- the problem in producing the perfect product lies in the difficulty of gelling the cosmetic oils that constitute the backbone of the majority of lip products.
- the most commonly used oils are typically polar, and achieving the desired level of viscosity and clarity is a complex matter.
- the usual viscosifying agents employed are waxes and /or clays; the end product achieved with the use of such materials is typically either too opaque or else less viscous and more oily-feeling that would be desired.
- the present invention relates to a gel-type topical composition comprising at least one cosmetically acceptable polar oil, and a gellant for the oil comprising at least one silica and at least one sugar fatty acid ester.
- the invention also relates to a method of gelling a polar cosmetically acceptable oil which comprises adding to the oil at least one silica and at least one sugar fatty acid ester, in an amount and under conditions sufficient to gel the oil.
- the compositions of the invention are soft, lubricious, transparent gels, viscous liquids or pastes that are particularly well adapted for use as a glossy top coat for a transfer resistant base coat or as a high shine lip gloss on its own.
- the invention also comprises a method of conferring shine to a skin surface which comprises applying to the skin surface a composition comprising at least one polar oil and a gellant comprising a complex of at least one silica and at least one sugar fatty acid ester.
- the base of the composition is a cosmetically acceptable polar oil.
- Cosmetically acceptable oil means one that is industry-accepted as safe for use on the skin surface to which the product is intended to be applied.
- Polar oils are frequent components of cosmetic compositions, and are distinguished from non-polar oils, such as hydrocarbons, by their relative lack of hydrophobicity.
- Polar oils typically contain heteroatoms, with higher electron negativity than carbon, e.g., alcohol residues, or an ester or triglyceride component.
- useful polar oils include, but are not limited to, vegetable oils and triglycerides (including hydrogenated liquid vegetable oils), such as castor oil, coconut oil, corn oil, jojoba oil, cottonseed oil, soybean oil, walnut oil, wheat germ oil, peach kernel oil, olive oil, peanut oil, sunflower seed oil, palm kernel oil, calendula oil, illipe butter, shea butter and caprylic/capric triglycerides; esters having the formula RCO-OR' wherein RCO represents a carboxylic acid radical and OR' represents an alcohol residue, such as isodecyl neopentanoate, tridecyl octanoate, cetyl palmitate, cetyl octanoate, cetyl stearate, cetyl myristate, isopropyl palmitate, isopropyl myristate, polyglyceryl-2-isostearate, neopentyl glycol distearate, isodecyl
- fatty alcohols such as lanolin alcohol, cetyl alcohol, isocetyl alcohol or oleyl alcohol.
- polar oils will normally constitute from about 10 to about 99% by weight of the composition, more preferably from about 30 to about 95% of the composition.
- lower quantities e.g., about 10% or less, are preferred to retain the transparent or translucent effect.
- Polar oils, particularly non-silicone polar oils are typically difficult to gel and retain the desired clarity.
- the hydroxide groups of the sucrose fatty esters interact via hydrogen bonding with the hydroxide groups on the surface of the silica particles, while the fatty acid portion of the ester molecule and the remaining hydroxide groups can interact with the polar oil components of the composition.
- the suspended silica serves as a physical cross- linking center while the fatty ester acts as a network spacer to form a gel phase.
- the success in this combination is particularly surprising in view of the general lack of success previously in producing a clear gelled polar oil. Any silica particle can be used in the gelling process, provided the particle is not fully surface- coated.
- the amount of silica used is not particularly critical, and can be employed in an amount of up to about 40% by weight of the composition, although the higher levels will produce a drier, less aesthetically pleasing product, and the higher levels necessary with particles having less exposed surface area do not viscosify as well as lower levels.
- the preferred silica employed in the gellant component is a fumed silica.
- fumed silica it is meant those high-surface area powdered silicas prepared by a pyrogenic process, e.g., during burning silicon tetrachloride in air (i.e., by the flame hydrolysis of silicon tetrachloride) and has a purity of 99.8% or greater.
- a pyrogenic process e.g., during burning silicon tetrachloride in air (i.e., by the flame hydrolysis of silicon tetrachloride) and has a purity of 99.8% or greater.
- submicron sized molten spheres of silica collide and fuse to form three dimensional, branched, chain-like aggregates, of approximately 0.1 to 0.5 microns in length. Cooling takes place very quickly, limiting the particle growth and ensuring the fumed silica is amorphous.
- Fumed silicas are available in untreated form, or with a surface treatment to render the silica more polar or non-polar. Although any type can be used, preferably the fumed silica used in the present invention is untreated, or at most partially treated. A fumed silica fully coated with non-polar materials will not provide the desired effect, although a silica coated with polar material, such as dimethicone copolyol, may provide some utility.
- the surface area of the fumed silica is preferably between about 90 to about 380m z /g, and most preferably is between about 200 to about 380m 2 /g.
- a particularly useful fumed silica is commercially available from Cabot Corporation under the trade name Cab-O-Sil M-5.
- a fumed silica is employed in an amount of about 0.2 to about 10% by weight, preferably about 1 to about 5%, of the total composition.
- the sugar fatty acid ester employed in the invention is a compound obtained by reacting a saturated or unsaturated C12-C22 fatty acid, preferably C16-C20, with a sugar or alkylsugar in which the alkyl group contains from 1 to 8 carbon atoms.
- the sugar is preferably a mono- or oligosaccharide.
- Examples of useful mono- or oligosaccharides include, but are not limited to, glucose, sucrose, galactose, fructose, lactose, mannose, maltose, trehalose, melibiose, raffinose, or ribose.
- a preferred sugar fatty ester is a fatty ester of glucose or alkylglucose.
- the fatty acid esters of alkylglucose are ethers of glucose in which the alkyl chain comprises from 1 to 8 carbon, atoms, preferably 1-4 carbon atoms.
- the preferred ester may contain a mixture of mono-, di-, tri- and tetraester derivatives with a proportion which may be of at least 50% by weight of mono- and diester derivatives and usually not exceeding 95% by weight of monoester derivatives relative to the total weight of the mixture.
- sugar fatty esters examples include, but are not limited to, sucrose monolaurate, glucose palmitate, alkylglucose sesquistearates, for instance methylglucose sesquistearate and alkylglucose palmitates, for instance methylglucose palmitate or ethylglucose palmitate, as well as the PEG or PPG derivatives of such compounds, for example, PEG-20 methyl glucose sesquistearate.
- Such compounds are widely available commercially, e.g., under the tradenames GlucateTM, GlucamTM, and GlucamateTM (Amerchol), GrillocoseTM (Grillo-Werke), and AntilTM(Goldschmidt).
- the amount of ester used in the composition will be from about 0.1 to about 10%, preferably about 0.5 to about 5%, by weight of the composition.
- the viscosity of the end product is dependent upon the ratio of the amount of silica to the amount of sugar fatty acid ester. Overall the ratio of these materials will range from about 10:0.5 to 0.5:5.0 silica to ester, with the lower amounts of the silica producing a lower viscosity product, and higher amounts of the silica producing a higher viscosity product.
- a product having a ratio of about 6:1 to 1:5, more preferably about 4.0: 1.0 -1:1, most preferably about 3:1-1:1, silica: ester is particularly preferred.
- the viscosity is also ultimately affected by the amount of gellant used relative to the amount of polar oil, with a higher viscosity achieved by a higher amount of gelling components.
- the viscosity is also affected by the polarity of the oils used, as the silica is more readily suspended in a more polar oil, presumably due to the interaction of the hydroxyl groups of the silica and the polar groups on the oils, so that a well-suspended silica can be used at smaller amounts than a silica that is not so readily suspended.
- the clarity of the gel can also be influenced by the amount of sugar ester used; although a more opaque gel still provides a gel system with unique and aesthetically pleasing properties, a transparent or translucent character is still preferred.
- the ester is then added to the mixture, mixed until dissolved, with continued mixing under the same temperature and mixing conditions, for several minutes (e.g., 30 minutes) until network formation is complete, which typically occurs at the point when all the components are dissolved.
- the product is then lowered to room temperature or to the desired pouring temperature.
- a particularly preferred component is one or more hydrocarbon polymers, particularly high viscosity liquid or paste polymers having a molecular weight of between about 400 to 6000 Daltons. While higher molecular weights can be used, they will tend to reduce the clarity of the product, resulting in a more translucent rather than transparent appearance.
- the hydrocarbon polymers are useful in conferring some additional viscosity, but also contribute to the feel of the product. In general, they confer a greater amount of tack to the composition, which in turn results in longer wear.
- materials useful for this purpose are linear or branched polybutene, polyisobutene, polyethylene, polydecene, hydrogenated derivatives thereof, and copolymers thereof, and mixtures of the foregoing. Particularly preferred is a hydrogenated polyisobutene. If used, the hydrocarbon polymer is used in an amount of about 1 to about 70%, preferably about 5 to about 50%, by weight of the composition.
- An additional optional component may be an oil soluble film-forming agent, for example, acrylate polymers, polyurethanes, linear or branched polyhydrocarbon film-formers.
- the film-former is typically used in an amount of from 0 to about 20% by weight.
- the composition may also contain oil soluble active agents and skin conditioning agents. Non- limiting examples of these materials include antioxidants, ceramides, fatty acids, sunscreens, emollients, oil soluble vitamins and plant extracts, and the like. When used as the oil phase of an emulsion, the composition can also contain water soluble actives. Depending upon its intended final use, the product may also contain a colorant.
- any type of pigment provided it is acceptable for use in the area to which the product will be applied, and with or without surface treatment, can be used in the product of the invention: examples of useful pigments include iron oxides (yellow, red, brown or black), titanium dioxide (white), zinc oxide, chrome oxide (green), chrome hydrate (green), ultramarines, manganese violet, ferric ferrocyanide, carmine 40, ferric ammonium ferrocyanide, or combinations thereof.
- Interference pigments which are thin platelike layered particles having a high refractive index, which, at a certain thickness, produce interference colors, resulting from the interference of typically two, but occasionally more, light reflections, from different layers of the plate, can also be added to provide a pearlescence to the product, is such is desired.
- the composition may also contain one or more types of cosmetically acceptable glitter, i.e., particles of transparent or colored, solid organic materials, such as poly(ethylene terephthalate), polymethacrylate, and poly(vinylbutyral), particles of metal, or particles of metal coated film or paper.
- Organic pigments may also optionally be included; these include natural colorants and synthetic monomeric and polymeric colorants. Exemplary are phthalocyanine blue and green pigment, diarylide yellow and orange pigments, and azo-type red and yellow pigments such as toluidine red, litho red, naphthol red and brown pigments.
- lakes are pigments formed by the precipitation and absorption of organic dyes on an insoluble base, such as alumina, barium, or calcium hydrates.
- Particularly preferred lakes are primary FD&C or D&C Lakes and blends thereof.
- Stains, such as bromo dyes and fluorescein dyes can also be employed.
- Pigments when used are typically present in an amount of about .1 to about 30%, preferably about 0.1 to about 20%, by weight of the composition.
- the gel system of the present invention can be used in the same manner as other gelling systems are in cosmetic compositions. Typical uses for gellant systems in cosmetics are structural support, prevention of liquid from flowing, controlled release of included agents, and the like.
- the gel system of the present invention provides all these functionalities, and may be used as a thickening component of any polar oil containing cosmetic, such as skin care creams, lotions, sticks or serums, as well as in color cosmetics, such as eyeshadows, blushes, mascaras, lipsticks, and the like.
- This polar-oil based gel can be used on its own, in an anhydrous product, or it can be used to thicken the oil phase of water and oil emulsion systems.
- the gel system is very useful as the base of a lip product. It has particular advantage when used in a moisturizing or shine-conferring top coat to a hydrocarbon- or silicone-based base coat (including, but not limited to, that described in US Patent No.
- 6340466 or 6019962 contents incorporated herein by reference
- Example 1 This example illustrates formulations of the compositions of the invention.
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- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Epidemiology (AREA)
- Birds (AREA)
- Chemical & Material Sciences (AREA)
- Inorganic Chemistry (AREA)
- Dispersion Chemistry (AREA)
- Dermatology (AREA)
- Cosmetics (AREA)
- Colloid Chemistry (AREA)
Abstract
La présente invention concerne un système de gélification qui comprend des quantités efficaces du point de vue gélifiant d'au moins une silice et d'au moins un ester d'acide gras et de sucre. Le système gélifiant selon la présente invention est utile pour gélifier des huiles polaires afin de produire des gels transparents ou translucides utiles dans des compositions topiques.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US51958303P | 2003-11-13 | 2003-11-13 | |
PCT/US2004/037016 WO2005048766A2 (fr) | 2003-11-13 | 2004-11-08 | Systeme gelifiant pour huiles transparentes |
Publications (2)
Publication Number | Publication Date |
---|---|
EP1686953A2 true EP1686953A2 (fr) | 2006-08-09 |
EP1686953A4 EP1686953A4 (fr) | 2007-08-29 |
Family
ID=34619361
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP04819057A Withdrawn EP1686953A4 (fr) | 2003-11-13 | 2004-11-08 | Systeme gelifiant pour huiles transparentes |
Country Status (7)
Country | Link |
---|---|
US (1) | US20050112161A1 (fr) |
EP (1) | EP1686953A4 (fr) |
JP (2) | JP2007511512A (fr) |
KR (1) | KR100794100B1 (fr) |
AU (1) | AU2004291053A1 (fr) |
CA (1) | CA2545456C (fr) |
WO (1) | WO2005048766A2 (fr) |
Families Citing this family (12)
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KR100876264B1 (ko) * | 2004-07-12 | 2008-12-26 | 이-엘 매니지먼트 코포레이션 | 고 광택, 무-번짐 입술용 제품 |
FR2888502B1 (fr) * | 2005-07-13 | 2009-06-26 | Oreal | Procede de maquillage et/ou de soin cosmetique |
WO2007007292A2 (fr) * | 2005-07-13 | 2007-01-18 | L'oreal | Produit cosmetique de maquillage et/ou de soin |
KR101404969B1 (ko) * | 2007-09-14 | 2014-06-19 | (주)아모레퍼시픽 | 오일과 폴리올이 함유된 화장료 조성물의 안정화 방법 및이를 이용한 화장료 조성물 |
WO2010035893A2 (fr) * | 2008-09-25 | 2010-04-01 | Kao Corporation | Préparation cosmétique à base d'huile |
KR20120062732A (ko) * | 2009-07-29 | 2012-06-14 | 리서치 파운데이션 오브 더 시티 유니버시티 오브 뉴욕 | 양친매성 에스테르를 사용하는 소수성 액체의 증점 방법 |
WO2013049599A2 (fr) * | 2011-09-30 | 2013-04-04 | Elc Management Llc | Composition de soins personnels comprenant un système d'émulsifiant naturel ne contenant pas d'agent émulsifiant à la silicone |
CA2927246C (fr) * | 2013-12-20 | 2022-08-16 | Colgate-Palmolive Company | Particules coeur-ecorce de silice et leurs utilisations en tant qu'agent antibacterien |
CA2927282C (fr) | 2013-12-20 | 2023-06-27 | Colgate-Palmolive Company | Produit de soin oral pour blanchiment des dents a base de particules de silice de structure coeur-ecorce |
KR101645277B1 (ko) * | 2014-12-05 | 2016-08-04 | 주식회사 불스원 | 젤쿠션의 제조방법 |
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JP7370752B2 (ja) * | 2019-07-17 | 2023-10-30 | 花王株式会社 | 油性固形化粧料 |
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JP3729788B2 (ja) * | 2002-03-25 | 2005-12-21 | 株式会社コーセー | 固形化粧料の表面模様付与方法及び該方法により得られる固形化粧料 |
JP4191976B2 (ja) * | 2002-10-18 | 2008-12-03 | 株式会社コーセー | 油性化粧料 |
JP2004210720A (ja) * | 2002-12-27 | 2004-07-29 | Kose Corp | 油性化粧料 |
JP2004292373A (ja) * | 2003-03-27 | 2004-10-21 | Kose Corp | 油性化粧料 |
JP2004300093A (ja) * | 2003-03-31 | 2004-10-28 | Kose Corp | 口紅オーバーコート |
JP2005068056A (ja) * | 2003-08-22 | 2005-03-17 | Kose Corp | 水中油型睫用化粧料 |
-
2004
- 2004-11-08 JP JP2006539683A patent/JP2007511512A/ja active Pending
- 2004-11-08 CA CA002545456A patent/CA2545456C/fr active Active
- 2004-11-08 WO PCT/US2004/037016 patent/WO2005048766A2/fr active Application Filing
- 2004-11-08 KR KR1020067010605A patent/KR100794100B1/ko active IP Right Grant
- 2004-11-08 AU AU2004291053A patent/AU2004291053A1/en not_active Abandoned
- 2004-11-08 EP EP04819057A patent/EP1686953A4/fr not_active Withdrawn
- 2004-11-10 US US10/985,781 patent/US20050112161A1/en not_active Abandoned
-
2010
- 2010-08-04 JP JP2010175182A patent/JP2010280692A/ja active Pending
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
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DE847901C (de) * | 1951-05-06 | 1952-08-28 | Franz Dipl-Chem Anders | Verfahren zur Herstellung von Gelees mit organischen hydroxyl-haltigen Stoffen |
EP0648496A1 (fr) * | 1993-10-15 | 1995-04-19 | Bristol-Myers Squibb Company | Compositions thérapeutiques pour usage dans le traitement des lésions de la peau et procédé de sa fabrication |
EP1277463A1 (fr) * | 2001-07-20 | 2003-01-22 | L'oreal | Composition moussante à base de silice et de polymère cationique |
Non-Patent Citations (1)
Title |
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See also references of WO2005048766A2 * |
Also Published As
Publication number | Publication date |
---|---|
EP1686953A4 (fr) | 2007-08-29 |
US20050112161A1 (en) | 2005-05-26 |
JP2010280692A (ja) | 2010-12-16 |
KR20060102559A (ko) | 2006-09-27 |
WO2005048766A2 (fr) | 2005-06-02 |
CA2545456C (fr) | 2009-09-22 |
JP2007511512A (ja) | 2007-05-10 |
WO2005048766A3 (fr) | 2005-08-11 |
CA2545456A1 (fr) | 2005-06-02 |
KR100794100B1 (ko) | 2008-01-10 |
AU2004291053A1 (en) | 2005-06-02 |
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